Oxidative Addition of Haloheteroarenes to Palladium(0): Concerted versus SNAr-Type Mechanism

Maes Bert U. W.; Verbeeck Stefan; Verhelst Tom; Ekomie Audrey; von Wolff Niklas; Lefevre Guillaume; Mitchell Emily A.; Jutand Anny

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Oxidative Addition of Haloheteroarenes to Palladium(0): Concerted versus SNAr-Type Mechanism

机译：卤代杂芳烃向钯（0）的氧化加成：协同作用与SNAr型机理

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The kinetics of the oxidative additions of haloheteroarenes HetX (X=I, Br, Cl) to [Pd-0(PPh3)(2)] (generated from [Pd-0(PPh3)(4)]) have been investigated in THF and DMF and the rate constants have been determined. In contrast to the generally accepted concerted mechanism, Hammett plots obtained for substituted 2-halopyridines and solvent effects reveal a reaction mechanism dependent on the halide X of HetX: an unprecedented SNAr-type mechanism for X=Br or Cl and a classical concerted mechanism for X=I. These results are supported by DFT studies.

机译：在THF中研究了卤代异芳烃HetX（X = I，Br，Cl）氧化成[Pd-0（PPh3）（2）]（由[Pd-0（PPh3）（4）产生）]的动力学。 DMF和速率常数已经确定。与通常公认的协同机制相反，针对取代的2-卤代吡啶的哈米特图和溶剂效应揭示了依赖于HetX的卤化物X的反应机制：X = Br或Cl的史无前例的SNAr型机理和经典的协同机理。 X = I。这些结果得到DFT研究的支持。

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《Chemistry: A European journal》 |2015年第21期|共8页
作者
Maes Bert U. W.; Verbeeck Stefan; Verhelst Tom; Ekomie Audrey; von Wolff Niklas; Lefevre Guillaume; Mitchell Emily A.; Jutand Anny;
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正文语种 eng
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arenes; homogeneous catalysis; kinetics; oxidative addition; reaction mechanisms;

机译：芳烃;均相催化;动力学;氧化加成;反应机理;

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1. Oxidative Addition of Haloheteroarenes to Palladium(0): Concerted versus SNAr-Type Mechanism [J] . Maes Bert U. W., Verbeeck Stefan, Verhelst Tom, Chemistry: A European journal . 2015,第21期

机译：卤代杂芳烃向钯（0）的氧化加成：协同作用与SNAr型机理
2. STEPWISE VERSUS CONCERTED MECHANISMS AT TRIGONAL CARBON - TRANSFER OF THE 1,3,5-TRIAZINYL GROUP BETWEEN ARYL OXIDE IONS IN AQUEOUS SOLUTION [J] . Hunter A., Rettura D., Taylor JA., Journal of the American Chemical Society . 1995,第20期

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4. C-C versus C-H Bond Oxidative Addition in PCX (X=P,N,O) Ligand Systems: Facility, Mechanism, and Control [C] . Boris Rybtchinski, David Milstein American Chemical Society National Meeting . 2004

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5. Mechanism of the palladium-catalyzed amination of aryl halides: Kinetic studies of the oxidative addition of aryl halides and sulfonates to phosphine complexes of Pd(0) and of the catalytic reaction of amines with aryl halides and base. [D] . Alcazar-Roman, Luis Manuel. 2001

机译：钯催化芳基卤化物胺化的机理：动力学研究氧化芳基卤化物和磺酸盐到Pd（0）的膦配合物中，以及胺与芳基卤化物和碱的催化反应。
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7. Reactivity and Mechanism in Oxidative Addition toudPalladium(II) and Reductive Ellmlnation from Palladium(IV)udand an Estimate of the Palladium-Methyl Bond Energy [O] . Byers PK, Canty AJ, Crespo M, 1988

机译：氧化加成的反应性及其机理钯（II）和钯（IV）还原还原 ud和钯-甲基键能的估计
8. Thermolysis of Anthracene Endoperoxides. Concerted versus Diradical Mechanisms. Microscopic Reversibility in Endothermic Chemiluminescent Reactions [R] . Turro, N. J., Rigaudy, J., Chow, M. F. 1978

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Oxidative Addition of Haloheteroarenes to Palladium(0): Concerted versus SNAr-Type Mechanism

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